Patent EA-000867-B1 (EA)
Title: Cyclic compound, process preparing therefor and process preparing diastereomers mixtures
Inventor: AKIBA TOSHIFUMI
IPC: C07C255/31
Filed: 1996-05-23
Abstract: A cyclic compound represented by formula (I):   wherein  n is an integer of 2 to 5; R1 represents a hydrogen atom or a substituent group represented by formula:   wherein R<a>, R<b> and R<c> each represents a phenyl, phenylmethyl or naphthyl group which may be substituted with at least one substituent group selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a halogen atom and a nitro group, a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms; and R<2> represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, with the proviso that a compound, in which n is 2, R<1> is hydrogen atom and R<2> is an ethyl group is excluded, and a salt thereof. 2. The compound or a salt thereof according to claim 1, which has the following configuration.   3. A compound represented by formula (II):   wherein  n is an integer of 2 to 5; and  R<1> represents a hydrogen atom or a substituent group represented by formula:   wherein R<a>, R<b> and R<c> each represents a phenyl, phenylmethyl or naphthyl group which may be substituted with at least one substituent group selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a halogen atom and a nitro group, a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms, and a salt thereof. 4. The compound or a salt thereof according to claim 3, wherein R, R and R are different from one another. 5. The compound or a salt thereof according to claim 3 or 4, which has the following configuration.   6. A compound represented by formula (III):   wherein n is an integer of 2 to 5; R<11> represents a substituent group represented by formula:   wherein R<a> R<b> and R<c> each represents a phenyl, phenylmethyl or naphthyl group which may be substituted with at least one substituent group selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a halogen atom and a nitro group, a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms, with the proviso that R<a>, R<b> and R<c> are different from one another, and a salt thereof. 7. The compound or a salt thereof according to claim 6, which has the following configuration.   8. A process for producing a cyclic compound represented by formula (I):   wherein  n is an integer of 2 to 5; R<1> represents a hydrogen atom or a substituent group represented by formula:   wherein R<a>, R<b> and R<c> each represents a phenyl, phenylmethyl or naphthyl group which may be substituted with at least one substituent group selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a halogen atom and a nitro group, a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms, with the proviso that R<a>, R<b> and R<c> are not hydrogen atoms at the same time; and R<2> represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, which comprises allowing a compound represented by formula (IV):   wherein n is an integer of 2 to 5 and R<2> represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, to react with hydrogen cyanide in the presence of a compound represented by the following formula (V) or a salt thereof: NH2R                            (V)   wherein R<1> represents a hydrogen atom or a substituent group represented by formula:   wherein R<a>, R<b> and R<c> each represents a phenyl, phenylmethyl or naphthyl group which may be substituted with at least one substituent group selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a halogen atom and a nitro group, a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms, with the proviso that R<a>, R<b> and R<c> are not hydrogen atoms at the same time. 9. The process according to claim 8, wherein R<a>, R<b> and R<c> are different from one another. 10. The process according to claim 9, wherein the compound of formula (V) is an optically single compound. 11. A process for producing a compound represented by formula (II):   wherein n is an integer of 2 to 5; and R<1> represents a hydrogen atom or a substituent group represented by formula:   wherein R<a>, R<b> and R<c> each represents a phenyl, phenylmethyl or naphthyl group which may be substituted with at least one substituent group selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a halogen atom and a nitro group, a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms, which comprises reducing the cyano group of a compound represented by formula (I):   wherein  is an integer of 2 to 5; R<1> represents a hydrogen atom or a substituent group represented by formula:   wherein R<a>, R<b> and R<c> each represents a phenyl, phenylmethyl or naphthyl group which may be substituted with at least one substituent group selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a halogen atom and a nitro group, a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms; and R<2> represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and subsequently effecting cyclization of the resulting amino compound. 12. The process according to claim 11, wherein R<a>, R<b> and R<c> are different from one another. 13. The process according to claim 12, wherein the compound of formula (I) is an optically single compound. 14. A process for producing a compound represented by formula (III-1):   wherein n is an integer of 2 to 5; R<1> represents a hydrogen atom or a substituent group represented by formula:   wherein R<a>, R<b> and R<c> each represents a phenyl, phenylmethyl or naphthyl group which may be substituted with at least one substituent group selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a halogen atom and a nitro group, a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms, which comprises reducing a compound represented by formula (II):   wherein n is an integer of 2 to 5; R<1> represents a hydrogen atom or a substituent group represented by formula:   wherein R<a>, R<b> and R<c> each represents a phenyl, phenylmethyl or naphthyl group which may be substituted with at least one substituent group selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a halogen atom and a nitro group, a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms. 15. The process according to claim 14 wherein R<a>, R<b> and R<c> are different from one another. 16. The process according to claim 15 wherein the compound of formula (II) is an optically single compound. 17. A process for producing a cyclic compound represented by the following formula (VI) or a salt thereof:   wherein n is an integer of 2 to 5, which comprises removing the substituent R<12> of a compound of formula (III-2):   wherein n is an integer of 2 to 5; R<12> represents a substituent group represented by formula:   wherein R<a>, R<b> and R<c> each represents a phenyl, phenylmethyl or naphthyl group which may be substituted with at least one substituent group selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a halogen atom and a nitro group, a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms. 18. The process according to claim 17, wherein the compound of formula (III-2) is an optically single compound. 19. A process for producing a diastereomer mixture of a compound represented by formula (I-1):   wherein n is an integer of 2 to 5; R<a>, R<b> and R<c> each represents a phenyl, phenylmethyl or naphthyl group which may be substituted with at least one substituent group selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a halogen atom and a nitro group, a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms, with the proviso that R, R and R are different from one another; and R<2> represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, which comprises treating an optically single compound of the compound of formula (I-1) in a protic solvent to effect the isomerization thereof. 20. The process according to claim 20, wherein the compound of formula (I-1) has the following configuration   21. The process according to claim 19 or 20, wherein said isomerization treatment is carried out under a heating condition. 22. The process according to claim 21, wherein said protic solvent is ethanol.